US4613596A - Amino methyl furans and pharmaceutical compositions - Google Patents
Amino methyl furans and pharmaceutical compositions Download PDFInfo
- Publication number
- US4613596A US4613596A US06/808,375 US80837585A US4613596A US 4613596 A US4613596 A US 4613596A US 80837585 A US80837585 A US 80837585A US 4613596 A US4613596 A US 4613596A
- Authority
- US
- United States
- Prior art keywords
- methyl
- nitroethene
- thio
- furfuryl
- dimethylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/12—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the present invention relates to new compounds with antiulcerative activity, the process for their preparation, and the pharmaceutical compositions which contain them.
- R is a piperidino, 4-methylpiperidino, (3-N-ethylpiperidinyl)-amino, 4-(2-hydroxyethyl)-1-piperazino, 4-benzyl-piperidino, 4-benzyl-piperazino, ethyleneimino, cyclopropyleneimino, cyclohexylamino, 1,4-cyclohexadienylamino, 1,4-cyclohexadienyl-2-methylamino, 1,4-cyclohexadienyl-2-ethylamino, hexamethyleneimino, (N-hexamethyleneimino)-amino, cycloheptylamino, cyclopentylamino, pyrrolidino, morpholino, endo-2-norbornylamino, or norbornen-2-ylamino, and
- the pharmaceutically acceptable salts comprise for example both non-toxic salts obtained by adding inorganic acids such as hydrochloric, hydrobromic, hydroiodic, phosphoric or sulphuric acid, and non-toxic salts obtained by adding organic acids such as maleic, acetic, citric, oxalic, succinic, benzoic, tartaric, fumaric, mandelic, ascorbic, methylsulphonic or ethylsulphonic acid.
- inorganic acids such as hydrochloric, hydrobromic, hydroiodic, phosphoric or sulphuric acid
- organic acids such as maleic, acetic, citric, oxalic, succinic, benzoic, tartaric, fumaric, mandelic, ascorbic, methylsulphonic or ethylsulphonic acid.
- the present invention also relates to a new process for preparing compounds of formula (I) as heretofore defined, and their pharmaceutically acceptable salts, characterised by reacting the compound of formula (III) ##STR2## with a compound of formula (II) ##STR3## in which R is as heretofore defined, at a temperature of 80° C., then isolating the compound obtained and, optionally, salifying it.
- the compounds of formula (I) as heretofore defined, and their pharmaceutically acceptable salts have proved useful in the treatment of affections requiring the administration of antagonists for receptors of histamine H 2 , such as the peptic ulcer or allergic skin symptoms.
- the present invention further relates to pharmaceutical compounds characterised by containing as their active principle an effective quantity of one or more compounds of formula (I) as heretofore defined, or their pharmaceutically acceptable salts, either as such or in union with other compatible active principles and/or with vehicles, diluents, solvents and/or pharmaceutically acceptable excipients.
- Table A given hereinafter contains, together with the meanings of R as heretofore defined, the corresponding structural formula of R and the symbol by which the corresponding compound of formula (I) is known hereinafter for brevity.
- the compounds of formula (I) and their pharmaceutically acceptable salts are active in the treatment of affections requiring the administration of receptors of histamine H 2 , such as the peptic ulcer or allergic skin symptoms.
- they have an antiulcerative activity which exceeds that of ranitidine or cimetidine, which are active principles already known in the art.
- they have an activity which is 1.1 to 1.3 times greater than ranitidine and 5 to 10 times greater than cimetidine.
- the compounds of formula (I) and their pharmaceutically acceptable salts offer the practical absence of side-effects.
- Acute toxicity was studied in male and female mice of Swiss stock, and in male and female albino rats of Wistar stock, by administering the active principle orally, intravenously and intramuscularly.
- the LD 50 and the relative reliability limits were calculated by the method of Litchfield and Wilcoxon (Pharmacol. Exp. Ther., 96-19, 1949).
- the subchronic toxicity test was carried out for each examined compound on 100 albino rats (Sprague-Dawley stock, 50 males and 50 females) having an average weight of about 120 grams.
- the rats maintained under standard environmental and diet conditions, were divided into 4 groups of 25 animals each, to which the dose given in Table 2 was administered intravenously (daily seven times per week for a treatment period of 4 weeks).
- test was also carried out on 10 adult dogs, 5 males and 5 females of Beagle breed having a weight of approximately 10 kg.
- the dogs maintained under standard environmental and diet conditions, were divided into 2 groups of 5 animals each, the first group (controls) being administered with a physiological solution over 4 weeks at a frequency of 7 times per week, and the second group being administered with the compounds AU/001-002-003-004-005-006-007-008-009-010-011-012-013-014-015-016-017-018-019-020 at a dose of 5 mg/kg, likewise over 4 weeks at a frequency of 7 times per week.
- the condition of the rats and dogs remained excellent, both in the case of the control animals and in the case of those treated with the products examined.
- Hematological, hematochemical, urine and hemato-pathological examinations remained within the norm. No variation occurred which could be imputed to the treatment effected with the aforesaid doses.
- the chronic toxicity test was carried out on 60 albino rats of Sprague-Dawley stock, of both sexes, having an average weight of 97 ⁇ 5 grams, and on 10 Beagle dogs of both sexes having an average weight of 10 kg.
- the treatment for the rats and dogs was effected orally (gastric probe for the rats) 7 times per week for 24 weeks with equal doses of all compounds from AU/001 to AU/020, as described in Table A, said doses being shown in Table 3.
- the daily oral administration of the examined compounds to the rat or dog produced no change in the hematological, hematochemical or urinal constants or in the macro or microscopic appearance of the main organs.
- the administered doses are in fact greater than the scheduled human therapeutic doses.
- the fetal toxicity test was carried out on 100 Sprague Dawley albino rats, 40 males and 60 females, having an average weight of 125 grams. Doses of 0, 25, 50 and 100 mg/kg of each examined compound were administered orally both to groups of 10 males, for a period of 60 days before copulation, and to groups of 20 females, for a period of 15 days before copulation.
- the tests were also carried out on 40 adult rabbits of New Zealand White stock of average weight 3 kg.
- the products were administered orally at doses of 0, 20, 40, and 60 mg/kg from the 6th to the 18th day of pregnancy.
- the administered doses are in fact greater than the scheduled human therapeutic doses.
- the test for evaluating cardiocirculatory effects was carried out on 6 male rabbits of New Zealand White stock having a weight of about 2.5 kg, and anesthetised by means of ethyl urethane, using doses of 100 mg/kg in the case of oral administration (3 animals) and 20 mg/kg in the case of intravenous administration (3 animals).
- the animals were treated orally either with doses of 1, 3, 10 and 30 mg/kg of the examined compounds, or with doses of 3, 10, 30 and 100 mg/kg of cimetidine, or with doses of 1, 3, 10 and 30 mg/kg of ranitidine.
- the activity of the examined compounds according to the present invention is approximately 3 times that of cimetidine, and 1.2-1.3 times that of ranitidine. All compounds from AU/001 to AU/020 as described in Table A were examined.
- a further two groups received cimetidine orally at doses of 10 and 20 mg/kg. Finally, before being placed in the retention cages, a further two groups received ranitidine orally at doses of 3 and 10 mg/kg.
- the animals which had fasted for 16 hours, were placed in retention cages for a period of 24 hours at a temperature of 21° C.
- the new compounds according to the present invention indicated by the symbols AU/001 to AU/020 in Table A, and administered orally in doses of 0.25 and 0.50 mg/kg and intravenously in doses of 0.10 and 0.20 mg/kg to male albino rats of Sprague-Dawley stock significantly reduce the volume of gastric secretion and gastric acidity, without causing alteration of the pH of the gastric juices.
- a cannula was inserted into the stomach of the animals for collecting the gastric secretion in accordance with the method of Ishii and Shinoraki, Jap. J. Pharmacol. 18, 93-1968, after ligature of the pylorus and the cervical region of the esophagus.
- the animals prepared in this manner received tetragastrin at a dose of 0.5 mg/kg by subcutaneous administration.
- the animals were treated either with a physiological solution (controls) or with the examined compounds by intravenous injection, at doses of 0.25 mg and 0.50 mg/kg.
- the hyperacidity induced by the tetragastrin administration was significantly inhibited by the intravenous treatment with the examined compounds. All compounds from AU/001 to AU/020 described in Table A were examined.
- the compounds of formula (I) and their pharmaceutically acceptable salts are particularly useful as active principles in the formulation of pharmaceutical compounds. Consequently, the present invention also relates to pharmaceutical compounds characterised by containing as their active principal an effective quantity of one or more compounds of formula (I) or their pharmaceutically acceptable salts, either as such or in union with other compatible active principles, and/or with vehicles, diluents, solvents and/or pharmaceutically acceptable excipients.
- Said pharmaceutical compositions can be formulated for administration orally, rectally, by injection or topically. They can for example be of solid form such as capsules, tablets, sustained-release tablets, single dosage sachets, suppositories or ointments, or in liquid form as solutions, suspensions or emulsions, for use either as such or for extemporaneous preparation. All the aforesaid pharmaecutical compounds can be formulated to contain diluents, vehicles, solvents and/or excipients well known to the art, and can be prepared by the methods well known to the art, fully described for example in "Tecnologia Farmaceutica", Silvano Casadio--Publ. Cisalpino Goliardica--Milan 1972.
- the new compounds according to the present invention can be administered either as such or in the form of pharmaceutically acceptable salts, in quantities from 0.2 to 50 mg/kg per day, and preferably from 0.5 to 20 mg/kg per day, and advantageously in stepped doses such as from 2 to 4 times per day in posological units which contain for example 10, 20, 30, 50, 100, 200, 250, 500 mg of active principle.
- the present invention also relates to the preparation of compounds of formula (I) and their pharmaceutically acceptable salts, which can be effected by reacting 2-[[[5-[(dimethlyamino)methyl]-2-furanyl]methyl]thio]ethylmethylsulphide of formula (III) ##STR24## with a compound of formula (II) ##STR25## in which R is as heretofore defined, at a temperature of 80° C., then isolating the compound of formula (I) obtained, then optionally salifying it.
- the compound of formula (II) can be prepared, according to a further subject matter of the present invention, by reacting 1,1-bis-(methylthio)-2-nitroethylene of formula (IV) ##STR26## with a compound of formula (V)
- R is as heretofore defined, and then with ammonia.
- This reaction can be usefully carried out in organic solvents, advantageously tetrachloroethane.
- the product obtained can be purified by passing it through a column of silica gel, followed by crystallisation.
- the compound of formula (III) can be prepared by the process described in Italian patent application 19473A/82 filed in the name of the same applicant.
- the obtained compounds of formula (I) can be easily isolated by the well known methods of the art, for example by crystallisation from solvents.
- these solvents are a water-ethyl alcohol mixture.
- the optional salification can also be conducted by the methods known to the art, for example by adding the suitable acid.
- the mixture is agitated for 2 hours.
- the solvent is evaporated under vacuum and the product obtained is purified through a silica gel chromatograph column. It is eluted with petroleum ether and then with dichloroethane.
- the product which separates is crystallised from diethylether, and melts at 121°-123° C.
- the product obtained melts at 125°-128° C.
- the product obtained melts at 118°-120° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and 4-(2-hydroxyethyl)-1-piperazine.
- the product obtained melts at 125°-128° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis(methylthio)-2-nitroethene and 4-benzylpiperidine, and then saturating with ammonia.
- the product obtained melts at 125°-128° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and 4-benzyl-1-piperazine, and then saturating with ammonia.
- the product obtained melts at 118°-121° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and ethyleneimine, and then saturating with ammonia. The product obtained melts at 98°-100° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and cyclopropyleneimine, and then saturating with ammonia.
- the product obtained melts at 111°-115° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and cyclohexylamine, and then saturating with ammonia.
- the product obtained melts at 115°-118° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and 1,4-cyclohexadienylamine, and then saturating with ammonia.
- the product obtained melts at 120°-125° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and 1,4-cyclohexadienyl-2-methylamine, and then saturating with ammonia.
- the product obtained melts at 125°-128° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and 1,4-cyclohexadienyl-2-ethylamine, and then saturating with ammonia.
- the product obtained melts at 120°-125° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and hexamethyleneimine, and then saturating with ammonia. The product obtained melts at 128°-132° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-methylthio)-2-nitroethene and cycloheptylamine, and then saturating with ammonia.
- the product obtained melts at 118°-125° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and cyclopentylamine, and then saturating with ammonia.
- the product obtained melts at 117°-124° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and pyrrolidine, and then saturating with ammonia. The product obtained melts at 120°-125° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and morpholine, and then saturating with ammonia. The product obtained melts at 120°-125° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and endo-2-norbornylamine and then saturating with ammonia. The product obtained melts at 130°-131° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and norbornen-2-yl-amine and then saturating with ammonia. The product obtained melts at 128°-132° C.
- Example 21 The procedure described in Example 21 is followed, but using equimolecular quantities of 1,1-bis-(methylthio)-2-nitroethene and N-amino-hexamethyleneimine, and then saturating with ammonia.
- the product obtained melts at 127°-131° C.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT20954/82A IT1190793B (it) | 1982-04-27 | 1982-04-27 | Composti attivi nel trattamento dell'ulcera e sintomi allergici della pelle |
IT20954A/82 | 1982-04-27 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06536730 Continuation | 1983-09-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
US4613596A true US4613596A (en) | 1986-09-23 |
Family
ID=11174566
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/808,375 Expired - Fee Related US4613596A (en) | 1982-04-27 | 1985-12-16 | Amino methyl furans and pharmaceutical compositions |
Country Status (8)
Country | Link |
---|---|
US (1) | US4613596A (hu) |
EP (1) | EP0092647B1 (hu) |
JP (1) | JPS6081177A (hu) |
AT (1) | ATE24904T1 (hu) |
AU (1) | AU563738B2 (hu) |
CA (1) | CA1223257A (hu) |
DE (1) | DE3369135D1 (hu) |
IT (1) | IT1190793B (hu) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4707550A (en) * | 1986-04-28 | 1987-11-17 | Ortho Pharmaceutical Corporation | N-(substituted thienyl)-N'-(substituted piperazinyl)-ureas |
US5229418A (en) * | 1990-04-26 | 1993-07-20 | Glaxo Group Limited | Carboxylic acid derivatives |
WO1998005317A1 (en) * | 1996-08-06 | 1998-02-12 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
US6177448B1 (en) | 1996-08-06 | 2001-01-23 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
US20050043386A1 (en) * | 2002-01-11 | 2005-02-24 | Sankyo Company, Limited | Amino alcohol derivatives or phosphonic acid derivatives and pharmaceutical compositions containing these |
US7910617B2 (en) | 2004-02-24 | 2011-03-22 | Sankyo Company, Limited | Method for suppressing the number of peripheral blood lymphocytes using an amino alcohol compound |
WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1196133B (it) * | 1984-06-06 | 1988-11-10 | Ausonia Farma Srl | Derivati furanici con attivita' antiulcera |
IT1180185B (it) * | 1984-06-12 | 1987-09-23 | Magis Farmaceutici | Derivato della ranitidina utile nel trattamento dell'ulcera |
ES2161212T3 (es) * | 1987-08-01 | 2001-12-01 | Takeda Chemical Industries Ltd | Aminas alfa-insaturadas, su produccion y uso. |
EP0760362B1 (en) * | 1994-05-18 | 2002-08-14 | Nisshin Seifun Group Inc. | diaminomethylidene derivative |
CA2342607A1 (en) * | 1998-09-22 | 2000-03-30 | Ishihara Sangyo Kaisha Ltd. | Medical composition containing nitroetheneamine derivative or salt thereof as active constituent |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4233302A (en) * | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
US4426521A (en) * | 1979-02-16 | 1984-01-17 | Eisai Co., Ltd. | Cyanoguanidine derivatives |
US4427685A (en) * | 1981-02-09 | 1984-01-24 | Beecham Group P.L.C. | Cycloalkylamino derivatives and their use in the treatment of peptic ulcers and the like |
-
1982
- 1982-04-27 IT IT20954/82A patent/IT1190793B/it active
-
1983
- 1983-02-03 AT AT83100992T patent/ATE24904T1/de not_active IP Right Cessation
- 1983-02-03 EP EP83100992A patent/EP0092647B1/en not_active Expired
- 1983-02-03 DE DE8383100992T patent/DE3369135D1/de not_active Expired
- 1983-09-29 AU AU19760/83A patent/AU563738B2/en not_active Ceased
- 1983-10-03 JP JP58183243A patent/JPS6081177A/ja active Granted
- 1983-10-06 CA CA000438490A patent/CA1223257A/en not_active Expired
-
1985
- 1985-12-16 US US06/808,375 patent/US4613596A/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4233302A (en) * | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
US4279911A (en) * | 1977-12-23 | 1981-07-21 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
US4304780A (en) * | 1977-12-23 | 1981-12-08 | Glaxo Group Limited | Aminoalkylthiophene derivatives as histamine H2 -antagonists |
US4426521A (en) * | 1979-02-16 | 1984-01-17 | Eisai Co., Ltd. | Cyanoguanidine derivatives |
US4427685A (en) * | 1981-02-09 | 1984-01-24 | Beecham Group P.L.C. | Cycloalkylamino derivatives and their use in the treatment of peptic ulcers and the like |
Cited By (14)
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US4707550A (en) * | 1986-04-28 | 1987-11-17 | Ortho Pharmaceutical Corporation | N-(substituted thienyl)-N'-(substituted piperazinyl)-ureas |
US5229418A (en) * | 1990-04-26 | 1993-07-20 | Glaxo Group Limited | Carboxylic acid derivatives |
WO1998005317A1 (en) * | 1996-08-06 | 1998-02-12 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
US6177448B1 (en) | 1996-08-06 | 2001-01-23 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
US6248785B1 (en) | 1996-08-06 | 2001-06-19 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
US7199150B2 (en) | 2002-01-11 | 2007-04-03 | Sankyo Company, Limited | Amino alcohol compounds |
US20050043386A1 (en) * | 2002-01-11 | 2005-02-24 | Sankyo Company, Limited | Amino alcohol derivatives or phosphonic acid derivatives and pharmaceutical compositions containing these |
US20070105933A1 (en) * | 2002-01-11 | 2007-05-10 | Sankyo Company, Limited | Amino alcohol compounds |
US7638551B2 (en) | 2002-01-11 | 2009-12-29 | Sankyo Company, Limited | Amino alcohol compounds or phosphonic acid derivatives thereof |
US20100035842A1 (en) * | 2002-01-11 | 2010-02-11 | Sankyo Company, Limited | Amino alcohol compounds or phosphonic acid derivatives thereof |
US8067396B2 (en) | 2002-01-11 | 2011-11-29 | Sankyo Company, Limited | Amino alcohol compounds or phosphonic acid derivatives thereof |
US8101650B2 (en) | 2002-01-11 | 2012-01-24 | Daiichi Sankyo Company, Limited | Method for treating a immunology-related disease |
US7910617B2 (en) | 2004-02-24 | 2011-03-22 | Sankyo Company, Limited | Method for suppressing the number of peripheral blood lymphocytes using an amino alcohol compound |
WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Also Published As
Publication number | Publication date |
---|---|
IT8220954A0 (it) | 1982-04-27 |
IT1190793B (it) | 1988-02-24 |
AU1976083A (en) | 1985-04-04 |
JPS6081177A (ja) | 1985-05-09 |
AU563738B2 (en) | 1987-07-23 |
ATE24904T1 (de) | 1987-01-15 |
DE3369135D1 (en) | 1987-02-19 |
EP0092647A1 (en) | 1983-11-02 |
JPH0429671B2 (hu) | 1992-05-19 |
CA1223257A (en) | 1987-06-23 |
EP0092647B1 (en) | 1987-01-14 |
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